That was shockingly easy. Flights to say Nassau are readily available in First using miles. Cash + points (4k points + $60 a night) is available at the Westin Bahamas. That having been said, figure out where you want to stay first. Then we can do flights. That's not the world's best hotel. If you've got the cash to drop, I'd go to the Ocean Club instead and use the free flights to get there. If not, we can consider other options. Do me a favor, click on my handle to the left and either e-mail me or PM me, and we can take this further. Preferably e-mail if you want quick replies.